Hey There, Cheerilee

by Silver Inkwell

Rating: teen
Tags: Original Character, Second Person, Other, Romance, Equestria Girls, Cheerilee, Random, Slice of Life, Human
Length: 4104

You are the main character. You have a crush on Miss Cheerilee. You want to ask her out on a date, but do You have enough courage to do that?

You are the main character. You have a crush on Miss Cheerilee. You want to ask her out on a date, but do You have enough courage to do that?

Rated Teen for many various random safety reasons.

Inspired by Wooden Toaster's/ Glaze's Love Me Cheerilee song on YouTube.

This is my very, very, VERY first Second Person story, so yes, please do comment down below.

Published 2017-02-27 20:30:01 UTC
Last updated 2017-02-27 20:30:01 UTC

Hey There, Cheerilee

Hey There, Cheerilee

You stare at yourself in the mirror, you examine your clothes.

Yep, you look good, you think to yourself.

Yep, you’re all ready to go, your tuff and things are in your backpack, your lunch is ready and packed, but there’s still just one more thing left to do…

Quickly you go over to your desk and grab the deodorant, apply it, and then spray some refresher on yourself. Yep, now you’re finally ready to go out.

You grab your backpack full of stuff and things and grunted, why did the teachers always have to make their backpacks heavy with lots of homework assignments? I mean did they want to cause all of them back problems? Seriously students needed some kind or sort of solution to this dire problem.

You walk slowly to school taking your time, after all, you only live less than three blocks away from it, you could literally take any form of transport there, well okay, maybe not any since riding on the back shell of a tortoise would be very slow indeed, quite so much that you would always constantly be late for all of your classes. With that thought in your mind you smiled very slightly, ah, you were just so glad that you had a very unique and special gift in always finding something positive in a situation no matter what it was, and comedy too of course. With a very big bright huge smile on your face you go down to Miss Cheerilee’s room where you see the crusaders talking to each other (or at least that’s what they liked to call themselves and you just had no opposition in the whole entire matter and thing, not that they would really truly listen to you anyways), there they were, Scootaloo, Apple Bloom, and Sweetie Belle, all grouped together like they were some kind or sort of cult, and yeah, sure their group was very tight, but surely it wasn’t quite that tight, right?

Anyhow they were talking together and you decide to sit down and wait for the rest of the class, and soon enough the rest of the others came in.

Twist, Pip, Featherweight, and other various random class members came through, the names of some which escaped your grasp. But as for the snotty rich kid Diamond Tiara and Silver Spoon, well thankfully they attended a private school after trying to come here but then declaring it was too ‘low class’ and ‘not proper enough’ for them quite yet. Ugh, you just wanted to punch them in their faces so badly and just see the looks and reactions on their faces afterwards, and any punishment like detention would have been so worth the price of it.

You smiled at this thought as the bell suddenly rand down and every student sat down knowing that if they didn’t Miss Cheerilee would tell them to do so.

“Alright class, settle down now, today we’re going to be learning about…”

Her words droned on and you completely miss what she said, but by the reactions and groans of your classmates you guess that it really isn’t that very good or fun at all. “Alright class, for this project and assignment I’ve put you in some very specific groups, Featherweight and Pip, you’re working together, and we also have Sweetie Belle and Scootaloo working together, Twist, you’re with Dinky, and Apple Bloom, you’re going to be working with him,” she said pointing at you. “Wait, me, are you sure this is a good idea?” you said.

“Yes, I am sure, now don’t complain and just do your work please.”

And with that said you went over to work with Apple Bloom even though you had no idea or clue what you were going to be doing exactly.

“Hey there,” she said plopping up unto the table (despite many warnings that tables were not for her butt, chairs were, tables were merely just for writing instead, but she and her friends continued to ignore them) with a bright big huge smile on her face, “I’ve seen you around here before, but are you new?”

“Yeah, I am, sort of, I mean kind of, look, I just came here to try it out okay? My last schools previously before this one haven’t exactly been kind or nice on me, and that’s not what I’m looking for. So yeah, I would really appreciate if you didn’t ask, but what are we working on here anyways?”

“Well, I won’t ask you about your past, but before I tell you what we’re working on I demand to know what your name is first, okay then?” she said.

Oh yeah, right, Miss Cheerilee didn’t call my name out, she just pointed instead.

“Um,” you say nervously stroking your hair to calm yourself down.

“Um? Your name is um?” she said giggling out loud trying to control herself to no avail, she laughed until you could finally get the chance and opportunity to speak again, but this time without any interruptions of any kind at all.

“Uh, no, it’s not, I’m so sorry, it’s-,” and then you quickly say your name.

“Well nice to meet you, we’re working on this chemical formula and a concept for a bridge design, and I’m really excellent and good at potions, art however, not so much really,” she said. “Don’t worry, I’m good at art, so how about you do the chemical formula and I’ll do the bridge thing, okay then?” you said holding out your hand for her to shake. “Deal,” she said spitting in her hand and then roughly grabbing your hand and shaking very hard. You just smiled at this, and while you thought that the whole entire idea and concept of spitting into one’s hand was very gross, weird, strange, unusual, and highly odd, it did reinforce the promise of any and all deals. Besides, you were well informed that they had quite the tendency to do that should the occasion ever permit them to do so, after all, it just wasn’t every day that you made deals.

You quickly went to work with the bridge design and soon enough you were done, and then you looked over to see Apple Bloom, and by the way she was just casually was leaned back in her chair you could guess that she was done.

“Done?” you say just to make sure and check her progress.

“Yep,” she said smiling with great pride, “You?”

“Yeah, I’m done, but what’s this for anyways exactly?” you say.

“Well the bridge and the chemical formula are designed to expand our creative and thinking minds respectively as Miss Cheerilee so kindly and gently puts it.”

You scoff at that statement in disbelief, “I don’t think that’s true exactly.”

“Well it doesn’t matter, we’re done and the rest of the class should catch up to us very soon,” she said just casually leaning her head back as I watched.

And she was right, soon enough the rest of the class did eventually catch up with them with varying mixed results of course, and then Miss Cheerilee went around collecting the assignment project. “Okay then class, it’s perfectly alright, just hand them in,” she said slowly making her way around until she got to them.

“I would appreciate if in the future that you didn’t do half of the work for the student,” she said taking all of the stuff and things in. “What was that all about?”

“Oh, I’m her teacher’s assistant, I help her out when she needs me.”

“Really? Well what’s that like, you know, being her assistant and all?”

“Well it’s quite nice, very much do indeed, I mean I’m so advanced and smart in all of my classes that I didn’t need to take math this year and I had a free period and legally I’m still required to be at school and I like being here early so I figured out why not help out others that are in need of help to fine their real true purpose? I mean because isn’t that the best thing to do, helping others out?”

“Yeah, I guess so,” she said looking down at the floor very thoughtfully.

“Yeah, well anyhow I help her out with whatever she needs me to do, getting her some coffee, grading some of her papers, and just helping out the students just like you in general, and best of all, I can get paid if I wanted to.”

“Wait, you’re not taking any money out of this deal?”

“No, not yet at least, I still have to make up my mind on that.”

“Oh, well then if you don’t take any of the money that would be very generous and kind of you,” she said. “Yeah, I know, and I am considering taking it, but what would I even use it for? My own wants and needs, or those of others instead? But I do think I may take some soon enough for my secret crush.”

“Ooh, you have a secret crush?” Apple Bloom said making some googly eyes at me, “Oh please just tell me who it is, I swear not to tell, I promise.”

You sigh, you knew that if you didn’t tell she would only just annoy you until you finally gave in and eventually told her, but now that you had her promise you knew that you could trust her since the Apple family always kept their word no matter what, or at least they tried to do so more than most regular ordinary people. “Alright, fine then, very well, as you wish, it’s Miss Cheerilee.”

Apple Bloom gasped, “No way, you have a crush on Miss Cheerilee?”

“Yeah, I don’t see what’s the big deal now, I’m eighteen now, a legal adult, I can do whatever I want now, and that includes dating her if she wanted to do that.”

“Yeah, well you can do whatever you want, but it doesn’t mean that you should.”

“Well guess what, I’ll still try, I mean I’ve always had a crush on her since the day I first saw her, I just wish that I could have spent more time in classes with her, because every moment that she’s around me it’s just like-,”

“Hey, don’t you start getting all poetic and philosophical on me just now yet, okay then? Because I will beat the shit out of you if you do.”

You blink in surprise and shock. “I’m an assistant, I could give you a detention for saying that so I would highly advise that you apologize to me about that remark and reflect upon your comments before blurting them out, okay then?”

She sighed, “Fine, alright then, I’m sorry for what I said to you back there then.”

You nod. “Alright, fine then, I believe you, just don’t ever let me catch you using language like that again in this classroom or school or else, okay than?”

“Alright, fine then,” she said grumbling to herself as she went over to sit by her best friends as the rest of the lesson went on while you just waited for it to be finally over and down with so that you could move on to your next classes.

You sat all alone just with your own thoughts and ideas until the class was finally eventually over. When it was, you go over to your next class, then the next after that, then lunch, and then afterwards you decide to go back to Miss Cheerilee.

“Hey there, Cheerilee,” you say entering the room very slowly.

“Nice to see you here, but tell me this please, what are you doing here exactly?”

“Uh, well I came to see you because I just need a tiny little bit of help with a small problem of mine,” you say sitting down at a desk.

“Oh, well can you tell me exactly what it is?” she said standing up.

“Well I would rather you come over here and take a look at it.”

“Okay then, fine, alright,” she said slowly coming over and leaning over to take a look at your papers while you licked your lips as you looked with lust at her breasts which now hung partially exposed since she was leaning over the desk to look at your papers, but you couldn’t see everything, and it was nothing too bad or exposing, but it definitely was and still would be inappropriate for most students. In your mind, you mentally slapped yourself and forced your eyes up to Miss Cheerilee trying not to stare at the delicious fruits that hung below her.

Now focused on her your attention suddenly snaps back to what she’s saying to you. “Hey there, are you even still listening to me?” she said now then.

“Uh, yeah, sort of, kind of, no, not really, I zoned out there for a moment.”

“Well try to stay focused, I’m trying to help you learn this stuff first, okay then?”

“Fine, alright then,” you say nodding as she took you through some of the steps and processes, but you already know all of this, all you wanted was just some time with her, and also a chance and opportunity to ask her out of course.

You try to resist the temptation to stare at her golden delicious apples, but you still couldn’t help to take a glance at them every now and then.

Eventually you finally manage to work up the nerve and courage for the question.

“Alright, I totally get this now,” you say suddenly stopping her, “Thanks.”

She smiled, “You’re welcome, just come to me any time that you need help and I’ll always be right here for you to give you whatever you want?”

“Well… I was wondering… if you would like to go out… well… uh…”

“Yes? What is it, come on, just spit it out for me now right now please.”

“Alright, fine then, do you want to go out on a date with me, please? Will you, please?” you say as you get on your knees pleading for her to agree with you.

She considered this for a very long moment with a look of deep focus and concentration on her face before she finally managed to respond eventually.

“Well… I really honestly don’ truly know, it would be very improper of me even if you technically aren’t my student anymore, but even disregarding that fact there is still the matter of our age,” she said. “Ah, don’t you worry about that, I’m eighteen now,” you said proudly puffing out your chest as you did so.

“Yes, that’s true, very much so indeed, but how could we even make this work out between us? You’re just barely an adult, and I’m still more than that.”

“Ah, don’t you worry about that, true love will always find a way.”

“Yes, that it does,” she said looking at you very carefully now then.

“Well then, what’s it going to be now? What’s your answer please?”

She looks at you for a moment, smiles very gently, softly, and warmly, and then says this, “Well I would love to, but I just don’t know if I can…”

“Oh, come on, what would be so wrong with you going out with me?”

She looks at you thinking for a very long deep moment, and then she sighs.

“Yeah, I guess that you’re right, or at the very least I suppose so instead.”

“Hey, that’s more like the spirit,” you saying gently patting her back very quickly.

“Well, what did you have in mind for the date though exactly?” she said.

“Uh, well I was thinking that we could do it on Friday after you’re done working of course,” you say. “That would work out quite well for me,” she said.

“Very well then, it’s settled, Friday at shall we say Six?”

“Yes, I agree, that’ll work out for me, but I guess that I’ll see you there then.”

“Yes, indeed, you will,” you say taking a very deep bow and then leaving her all alone as you go out the door, room, and school back to your own house.

Friday eventually came finally and you went to school just like you always do, after school you quickly go back home and change into more formal attire.

You decide to freshen up and then go over to meet her at her house.

You ring the doorbell and wait very nervously for her.

Eventually she finally comes out wearing a very sexy red dress.

“Hey there, handsome, am I wearing too much or is it just enough instead?”

You stare at her trying not ot make your jaw drop down, but it was no use as your moth slightly opened and gasped with great shock and surprise.

“Uh, wow, I had no idea that you could be so damn hot and sexy,” you said.

She laughed at this comment and smiled at you, “You’re cute and funny, perhaps we can make this work out, but for now I just want some food right now, okay then?” she said holding out her hand for you. “As my lady wishes.”

And with that said you take her hand and slowly gently guided her to your car opening the passenger door and then going around to your own side.

“Huh, it looks like you’re not only a gentleman but that you can also drive too as well,” she said. “Yeah, well I can, I just don’t because school is just so close to me, too close, I mean that’s why I decide and choose to walk there every day after all, but yeah, I’ve been driving ever since when I turned sixteen or around then.”

“Oh, well then, I guess that makes you even more of a man than I previously thought of you beforehand, but please tell me this, where are we eating exactly?”

“We’re going to be doing Italian spaghetti tonight, I hope that you don’t mind.”

She smiled. “No, I don’t I just love Italian spaghetti and meals.”

“Well then, I’m sure that you’ll enjoy tonight.”

And with that said you slowly drive off to the restaurant and sit down at a table.

“Don’t worry, I already reserved seats for us, and the meal is on me since I know how low Teacher’s salaries can get and I don’t really have any plans for this money since I’m still technically living with my parents right now.”

“Oh, you don’t have to do all of that for me.”

“Nonsense, it would be my genuine pleasure, just ask for anything that you want and don’t worry about money or having too much,” you say.

She smiled at you and then ordered her meal from the waiter and then it was your turn. While you two were waiting for the food to come back you decide to talk while sipping some of your drink. “So, Cheerilee, what’s your favorite color?”

“Oh, you don’t need to call me Cheerilee, but it’s red.”

“Oh, very good then, mine is -,” you say.

“Ah,” she says. “Favorite ice cream?” you say trying to keep the conversation moving forward. “Strawberry,” she says. “Oh, well then, very good, mine is-,”

“That’s nice, but while I want to, and honestly must and have to thank you for all of this I don’t think it would be very appropriate to be dating my assistant even if he wasn’t a student of mine technically enough, even if you just went to the same school where I taught, which you still do, well that would make it very awkward for me and put us both in a very difficult situation…”

It takes a very long moment before this finally fully sinks into your mind and head, “Oh, so you’re saying that you won’t date me because it would make us look bad? That it would make you look bad?” you say glaring at her very angrily trying to accept what she has just said. “Well yes, sort of, kind of, look, I don’t think that it would be good for you to date any teachers at the school, I mean you should try it first with other people around your own age, right?”

“Yeah, I guess I should, but honestly how old are you anyways?”

She looked down at the table, “Not that much older than you…”

“Exactly, we can still make this work out, but only if you are willing and ready to, so I’ll need you to be 100% in on this, do you understand that?”

“Yes, I do,” she says as the food suddenly arrives. “Good then, because I really like you, I have ever since the day that I first saw you in the school here.”

“Look, not to be rude, but you can’t just judge people on their looks.

“Oh, trust me, I’m not, I’ve taken the time and I’ve gotten to know you quite well just by studying how you act in and out of class, and it’s really quite interesting.”

“So, what are you saying then? That you won’t date anyone else? Is that it?”

“Well no, not exactly, look, I do want to date you, but I think that because I might love you that your own happiness means even more to me, so if you don’t want to do this just say so now, we’ll eat our meal and then leave as we were before all of this,” you say. “No, I don’t want to do this, but maybe after you’re done with school I’ll think about it, but no promises though,” she says smiling.

“Oh, clever girl, alright, fine then, but for now let’s just eat, shall we?”

And with that said you both dive into your meals determined to enjoy it.

When you were finally eventually done, and her as well too of course, you pull out a card and pay for the meal. “Aren’t you going to leave a tip?”

“Oh no, I never do, tipping is a very stupid thing to do, I mean why can’t we just expect the food companies to pay their employees a reasonable and fair amount of money for what they do? Seriously tipping has infected the mind of every person in our nation and it’s a problem that needs to be fixed very soon.”

“Wow, are you always so well informed about such small tiny little matters?”

“Yes, and speaking about food and money people need to add to their spices and have more than just pepper yes to salt, but anything but pepper.”

She shook her head at you. “I can’t tell if you’re crazy or insane.”

You smile at that, “Why can’t it be both at the same time?”

She smiled, “Yeah, I guess that you’re right about that, but I guess that I’ll see you at school on Monday then?” she said looking at you very fondly now then.

“Yeah, I guess so, unless something happens to me, but I highly doubt that ever possibly happening, I am after all, a very careful man,” you say opening the car door for her again, then going around and driving her home. “Well then, I enjoyed our date, just don’t ask me to do it again anytime soon, okay then?”

“Very well then, fine, alright my lady, but do I not get a farewell kiss?”

She laughed, “No, not yet, but maybe should we ever do this again.”

“Well then, I look forward to that day,” you say turning around.

Then you wave her goodbye and drive off into the distance out of her sight back to your own home, take off your clothes and then lay in your bed.

Well, that was a failure, but at least there was always tomorrow, or rather Monday instead, and there were still plenty of girls left in the school.

Sitting up you take out some pictures of seven girls and hung them on your dartboard and then got out your darts. “Alright, fine then, who shall it be this time?” you saying covering your eyes and blindly throwing a dart.

You slowly open your eyes to see that the dart had landed on Twilight Sparkle.

“I had half hoped for Rarity or Sunset Shimmer, but fate has decided upon you my fair lady, and so I shall wait until Monday to try out my luck.”

And with that said you smiled, took down the dartboard and pictures, and then eventually went off to bed and slept with dreams of your next girl.